Why Choose Keith Thomas
• 20 years of experience as a Senior Apple Support Specialist at Apple Computer UK HQ.
• Former Apple Computer UK Mac Support Specialist and Apple Authorised Service Provider background.
• Established and Independent since 2010 for on‑site Apple Support Service – no call centres, no outsourcing, no hardware repairs. Over 25,000+ Apple problems resolved. Unique on-site Apple Support Service. backed up with Independent Apple Telephone Support Assistance.
• Trusted by home users, small businesses, and professionals across London and the South East UK.• Clear, honest, software‑only support. No Hardware Repairs. Expert Apple Consultancy Service.
On‑site Apple Mac Support in London and the South East UK
What this page covers
This guide explains the real reasons a Mac cannot send emails, the steps you can try yourself, and when it’s time to get professional on‑site help. It applies to:
• Apple Mail
• Outlook for Mac
• Gmail, iCloud, Outlook.com, Yahoo and IMAP accounts
• Microsoft 365 and Exchange accounts
If your Mac won’t send emails, shows outgoing server errors, keeps messages stuck in Outbox, or asks for your password repeatedly, this page is for you.
The most common reasons a Mac cannot send emails
These are the issues that Keith Thomas identifies most often during on‑site visits:
• Incorrect outgoing mail server settings
• Authentication issues
• Incorrect password
• Microsoft 365 or Google security blocks
• Damaged Mail or Outlook preferences
• macOS update issues
• Keychain conflicts
• Corrupted user account
Quick checks you can do yourself
These steps solve around 60% of sending issues.
Check 1 – Restart the Mac
A restart resets Mail, Outlook and network services.
Check 2 – Restart the Mail or Outlook app
Fully quit the app and reopen it.
Check 3 – Check your password
Sending often fails after password changes.
Check 4 – Turn Wi‑Fi off and on
This forces the Mac to reconnect to the mail server.
If emails are stuck in the Outbox
This usually means:
• Incorrect outgoing server settings
• Authentication failure
• Network issue
Try:
• Mail → Settings → Accounts → Server Settings
• Restarting the Mac
• Turning Wi‑Fi off and on
If Mail shows “Cannot Send Message Using the Server”
This usually means:
• Wrong SMTP server
• Server offline
• Authentication issue
Try:
• Selecting another outgoing server if available
• Restarting the Mac
• Updating macOS
If Outlook for Mac cannot send emails
This usually means:
• Damaged Outlook profile
• Microsoft 365 authentication issue
• Keychain conflict
Try:
• Removing and re‑adding the account
• Restarting the Mac
• Updating Outlook
If Gmail cannot send emails
This usually means:
• Google security block
• App permissions revoked
• Incorrect password
Try:
• Approving the login on your phone
• Checking Google Account security alerts
• Restarting the Mac
If sending issues started after a macOS update
This usually means:
• Mail database reset
• Keychain reset
• Account re‑authentication required
Try:
• Re‑entering your email password
• Restarting the Mac
• Updating all apps
If sending works on another user account
This usually means:
• Corrupted user account
• Damaged Mail or Outlook preferences
• Permissions issues
Try:
• Testing sending on another user account
• Restarting the Mac
• Reinstalling macOS without erasing data
When DIY stops working
You should get on‑site help if:
• Emails refuse to send at all
• Outgoing server errors keep returning
• macOS reinstall does not fix the issue
• Mail or Outlook crashes during sending
• You need your data preserved
These issues usually require:
• Email account and server configuration repair
• macOS recovery
• Data‑safe macOS reinstall
• User account repair
• Permissions and system file diagnostics
On‑Site Apple Mac Support – London & South East UK
If your Mac cannot send emails, Keith Thomas provides an often same‑day on‑site support service across:
• Central London
• West, North, South and East London
• Surrey
• Berkshire
• Hampshire
• Wiltshire
Keith Thomas is a Mac Support Specialist in:
• Email sending and server issues
• Apple Mail and Outlook configuration
• macOS configuration repair
• Data‑safe macOS recovery
• macOS reinstall and repair
• New Mac setup and migration
• User account and permissions diagnostics
Book on‑site help in London and the South East UK
If your Mac cannot send emails, Keith Thomas can visit your home or office and get you working again.
Keith Thomas – Apple Mac Support Specialist
Established 2010 – Open 09:30–20:30, 7 Days
Contact Keith Thomas by Telephone: 07800 940756 or by Text to: 07800 940756, or simply complete an online website contact form 24/7